“Wait, we found more Roosevelt kids?”

~The Writer of Teddy’s Tots

We’re not exactly shy here about our preferences when it comes to the Roosevelt presidents. We’re Team Teddy all the way. But we’re not haters on this front. We’ll readily admit that FDR did have his badass moments, and his wife Eleanor was no slouch on that front either. So while we’re not surprised that their offspring generally went ahead and did impressive things, we were pretty amazed to hear about Eleanor’s supposed “favorite son”, Elliott.

To give you a sense of the Elliott Roosevelt, um, flavor, we’ll just say that we’re about 90% certain that Elliott Roosevelt is only considered her favorite son because he made that claim after she died. Strap in, you guys, this is going to be a wild one.

Now let’s take a moment to talk about the middle son of FDR who, well, let’s just say lived a colorful life.

Elliott Roosevelt Might Just Be the Most Interesting Roosevelt Not Named Teddy

Franklin Delano Roosevelt and Eleanor Roosevelt were directly responsible (via doing it) for the creation of six individuals to enter this world. Anna was the oldest, and the only daughter, who wrote a few children’s books in the 30s, and was appointed to several presidential commissions on women and human rights by John F. Kennedy.

Then came James, who served in the House of Representatives for ten years and earned the Navy Cross during World War II. Franklin passed way as an infant, while Franklin Jr. also served in the House, and John, the youngest, was the only to never seek political office, working primarily as a businessman. But smack dab in the middle we had Elliott, born in 1910 and named after his maternal grandfather.

From the beginning Elliott operated under a different set of rules than the rest of his family. After attending prep school at Groton (much like all of his brothers), he refused to attend Harvard.

We’re going to assume he was actually offered admission to Harvard before turning it down, because if not, um, yeah Elliott, everyone on our staff refused to attend Harvard anyway. We were like, ugh, Harvard totally wants us, but we don’t got time for that. Eat our dust, Harvard, and while we’re at it, Princeton? Yeah, we’re turning you guys down too.

Anyway, instead of attending college, Elliott jumped right into the workforce, where he worked a few jobs here and there before snagging a spot as manager of the Hearst radio chain at the ripe age of 23 in 1933.

Did he almost certainly play up his family name to get this job, much to the chagrin of the rest of his family who he was often at odds with? Listen, we’re pretty sure dead people can’t sue us for libel, so sure, we’re going to say he fucking did.

That isn’t to say he was some nepotistic sycophant, as he eventually left that job to join the Air Force, where he would serve from 1940 to 1945 before getting discharged with the eventual rank of Brigadier General.

General Elliott Roosevelt, pictured here holding in a fart.

Roosevelt’s military history was a combination of badass and batshit crazy, swirled together with corruption-tinged sprinkles. He flew on 89 combat missions despite being classified as 4-F, or unfit for flight, due to his poor eyesight, largely flying on reconnaissance and photography assignments.

Because, you know, it’s not like you need keen vision to fly fucking reconnaissance missions. He commanded several different flight units, and accompanied his father as a military aide to the famous Casablanca meeting of 1943, as well as the Cairo-Tehran Conference of 1944, before serving his last day before discharge on VJ-Day.

Oh and one time in 1943 he was accused of letting Howard Hughes bribe him into recommending that the eccentric Billionaire receive a contract for the Hughes D-2 twin-engine (wooden) woodcraft, instead of the much superior Lockheed XP-58 Chain Lightning. Which, let’s be honest, he absolutely did get bribed—Hughes spent the modern-day equivalent of $72,000 entertaining Hughes, and set him up with the actress Faye Emerson, who Roosevelt promptly left his wife for.

Pictured, Roosevelt and Emerson…proposing a threesome?

Oh, and speaking of wives, we know you’re wondering, did Elliott Roosevelt fuck? Folks, he did indeed. He had five kids over the course of his five marriages, and once he shed one wife he wasted no time finding another. His first marriage lasted a year, and then a few months later he married Ruth Googins, with whom he had three children before leaving her for Faye Emerson, the actress Hughes set him up with, then known as “The First Lady of Television.” He divorced Googins in March of 1944, and married Emerson on December 3^rd of that year, but don’t feel bad for Googins. She herself re-married just three months after the split.

After divorcing Emerson, he waited a whole year before marrying Minnewa Bell in 1951. He stayed with her a full nine years, then pulled one last patented “divorce and new marriage in the same calendar year” in 1960, leaving Bell and marrying Patricia Peabody Whitehead, with whom he stayed with for the next thirty years.

Roosevelt with wife number five. Again, Elliott Roosevelt fucks.

After the war, he tried his hand at a variety of different schemes, but mostly just lived off his mom’s money. Yup, pretty much for as long as Eleanor Roosevelt was alive and well, she covered his ass financially. In fact, a lot of his financial standing came either directly or indirectly from his parents.

Not only did Eleanor Roosevelt fund his particular enterprises, he also traded heavily on the Roosevelt name. In 1946, he wrote As He Saw It, which discussed his experiences as FDR’s aide. It was, um, let us say, a little too pro-Soviet Union for some people to stomach? Also, there’s no good way to include this nugget, so we’ll just drop it here—at a dinner during the Tehran Conference, Joseph Stalin casually suggested that after the war ended, they should round up and execute some 50,000 German officers and technicians, so that they could be unable to wage war again.

While Winston Churchill responded to that by saying “I would rather be taken out into the garden here and now and be shot myself,” Elliott Roosevelt was like, “Actually that seems like a good idea there, Joe!” So yeah. Despite that, Eleanor Roosevelt wrote the dedication to As He Saw It, as well as for the four volumes of FDR letters he edited and published.

After Eleanor Roosevelt passed away in 1962 he did start earning money on his own, which is to say he allegedly did some shaaady shit. After a brief stint as the Mayor of Miami Beach, Florida from 1965 to 1967, he launched a business career mostly notable for its many alleged ties to organized crime.

These weren’t just idle whispers, they were serious enough that he was investigated by the Senate in 1973. Now what did this committee allege? That he straight up offered to pay $100,000 to assassinate the Prime Minister of the Bahamas! What!? Jesus! That’s a fucking heel turn if we’ve ever seen one!

Is that fucking insane, and so over-the-top that you’re wondering how there’s not been a movie made about Elliott Roosevelt yet? Absolutely. But that’s not even the end of it, since what he did with his later years was somehow almost as comically nuts.

While he managed to steer clear of, you know, writing a “the rest will come after the job is done” $10,000 check to an alleged mobster front man to have Lynden Pindling killed because he refused to issue a gambling license to an associate of his, he decided to pursue a different, but equally mind-blowing career.

If you had to pick one profession to associate with Elliott Roosevelt, you’d probably go with “writer.” He wrote many books throughout his life, including the previously mentioned memoir and books of letters, but for some reason, starting in 1984 at the age of 74, he started publishing a series of mystery novels where his mother, Eleanor Roosevelt, solved crimes and murders while serving as the First Lady.

That is absolutely incredible and one of the strangest things we’ve ever encountered the more we think about it. First of all, writing a murder mystery novel starring the First Lady is not something you would ever consider doing. Equally as unfeasible would be writing a murder mystery novel starring your mother. If you combine that together you have something that’s just about the most impossible thing we could ever imagine. Though, there is one literary feat that is even more unfathomable than that.

WRITING NINTEEN OF THOSE FUCKING BOOKS! And most of these came out after Elliott Roosevelt passed away in 1990. Which means there was enough interest to just keep churning these out, including a 20^th book in the series that’s ghostwritten by someone else!

So really, let’s just take a second to step back and marvel at this. Elliott Roosevelt, the second oldest son of Franklin Delano Roosevelt, wrote 19 books about his mom solving murders in the White House, which if anything is a jarring reminder of how much free time we used to have before the internet.

This is after he met a wife while being bribed by Howard Hughes, which he did during his tenure of flying planes for the military that he straight up was not physically qualified to fly, and later, for funsies, he managed to work a failed assassination attempt of a foreign politician in there. We hate to say it, but this might be crazier than anything any of Teddy Roosevelt’s children ever managed to do. We’re as stunned as you are.

Elliott Roosevelt passed away at the age of 80 from heart failure, and to hear him say it his one biggest regret was that he didn’t get to die after his older brother James, because he apparently hated James. But it’s fair to say he definitely managed to not be boring. So here’s to Elliott Roosevelt, son of Franklin and Eleanor, and one of the most mind boggling people we’ve ever covered on this site.